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通过香豆素对胺进行酰化高效合成酪氨酸衍生的海洋海绵代谢产物。

Efficient synthesis of tyrosine-derived marine sponge metabolites via acylation of amines with a coumarin.

作者信息

Harburn J Jonathan, Rath Nigam P, Spilling Christopher D

机构信息

Department of Chemistry and Biochemistry, University of Missouri-St. Louis, One University Boulevard, St. Louis, Missouri 63121-4499, USA.

出版信息

J Org Chem. 2005 Aug 5;70(16):6398-403. doi: 10.1021/jo050846r.

DOI:10.1021/jo050846r
PMID:16050702
Abstract

Condensation of N-acetylglycine with aldehyde 15 in acetic anhydride gave acetamido coumarin 16. Hydrolysis to the enol coumarin 17 and reaction with hydroxylamine gave the oximino coumarin 18. Reaction of the oximino coumarin 18 with a range of nucleophiles gave the phenolic oximes in excellent yield. The rates of acylation of histamine with the oximino coumarin 18 and methyl ester 9 were compared. Oxidative spirocyclization of three representative phenolic oximes with polymer-supported (diacetoxyiodo) benzene gave the spiroisoxazolines.

摘要

N-乙酰甘氨酸与醛15在乙酸酐中缩合得到乙酰氨基香豆素16。水解为烯醇香豆素17并与羟胺反应得到肟基香豆素18。肟基香豆素18与一系列亲核试剂反应，以优异的产率得到酚肟。比较了组胺与肟基香豆素18和甲酯9的酰化速率。三种代表性酚肟与聚合物负载的（二乙酰氧基碘）苯进行氧化螺环化反应得到螺异恶唑啉。

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